Oxidation of Cyclohexanone to Adipic Acid Essay

994 Words May 8th, 2013 4 Pages
April Goodson
CHEM 242L-002
February 20, 2013

Oxidation of Cyclohexanone to Adipic Acid
Abstract
The cyclic ketone cyclohexanone was oxidized to adipic acid using the oxidizing agent nitric acid. The experiment yielded 0.2667 grams of adipic acid, giving a percent yield of 113.97%. Although the product was allowed to dry for one week, residual moisture was still present in the sample and a melting point could not be obtained. This error in the experiment either resulted from adding too much water or not allowing the product to remain in the Hirsch vacuum filtration for long enough to sufficiently dry.
Introduction
Redox reactions are an important class of reactions in organic chemistry that involve the transfer of electrons from
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Nitric acid has the chemical formula HNO3, a molecular weight of 63.01 grams/mol, a melting point of -42 °C, and a density of 1.5027 grams/mL. (PubChem.com)
The product yielded in this reaction was adipic acid (Figure 1), a white crystalline solid substance at room temperature, which can be deprotonated twice. Adipic acid is an important industrial chemical used in the synthesis of nylon. Adipic acid has the molecular formula, C6H10O4, the molecular weight 146.14 grams/mol, a melting point of 153 °C, and a density of 1.36 g/cm3. (PubChem.com)
Figure 1. Reaction mechanism for the reduction of cyclohexanone to adipic acid, using the oxidizing agent nitric acid.
Figure 1. Reaction mechanism for the reduction of cyclohexanone to adipic acid, using the oxidizing agent nitric acid.

Experimental
This experiment was conducted under conditions described by Williamson, 2003. To begin, approximately 150 mg of cyclohexanone was placed into a vial. In a separate 10 x 100 mL reaction tube, 1.0 mL of HNO3 was added by pipette, along with a pre-weighed boiling chip. The reaction tube containing the nitric acid was clamped into a sand bath under the fume hood and heated at a low setting. One drop of cyclohexanone was careful added to the nitric acid. The presence of a brown oxide indicated that the reaction had begun, at which point the reaction tube was removed from the sand bath.…

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